Holiday houses in Deal Island Historic District

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Top-rated holiday rentals in Deal Island Historic District

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Guest favourite
The exterior of a three-story house is displayed, featuring a white facade with blue accents on the roof. A bay window is visible on the second level, framed by lush greenery, while a small flower bed is positioned in front. The property is surrounded by a well-maintained lawn.
Home in Deal Island Historic District
5 out of 5 average rating, 17 reviews

The Tangier Escape

Looking for a relaxing getaway, or duck hunting or fishing lodging ? This coastal themed home is located in a quiet crabbing village on Deal/Wenona Island MD The house has 2 bedrooms UPSTAIRS which has a King size bed in one room and then a Queen size bed in the other. . Downstairs, there is a sofa bed that is a queen size pullout bed. There is a fully equipped kitchen with a griddle and a large pot for cooking fresh crabs in. There is also a grill to cook up any fish caught that day.

Guest favourite
An outdoor fire pit is surrounded by several black adirondack chairs, creating a cozy gathering space. The scene is set against a backdrop of lush trees and St. Leonard's Creek, with dusk settling in and a soft blue hue filling the sky.
Cabin in Lusby
4.91 out of 5 average rating, 252 reviews

Hideaway on the Bay: Waterfront Vintage A Frame

The Hideaway on the Bay is a waterfront A frame where you can disconnect from the things that can wait so you can connect with the people who matter most. A place where kids fall in love with nature, and where old friends make new memories. The house is a 2 bed 1 bath 1974 flat top A Frame that sits on two acres on the outskirts of Lusby, MD—and a low traffic hour(ish) drive from the DMV. Enjoy the indoor fireplace, outdoor fire pit, swinging chairs, kayaks, canoe, fish, and catch crabs --

Top Guest favourite
A serene outdoor area is depicted, featuring a well-maintained lawn and stone pathway leading towards the water. The view overlooks a marina with boats docked, surrounded by trees and residential properties. Comfortable lounge chairs are positioned on a deck, inviting relaxation.
Home in Solomons
5 out of 5 average rating, 128 reviews

The Little House on Back Creek

Get away and relax at this peaceful, very private and centrally-located home in the heart of Solomons Island on Back Creek with beautiful water views overlooking Solomons Harbour. The property is shared with Jacqueline Morgan Day Spa and The Blue Shell Gifts and Décor. Just a quick walk to a enjoy a massage, facial, mani/pedi, salon services and shopping! Enjoy fishing, kayaking, bicycling, walk to so many great restaurants nearby and bring your boat! Docking is available during your stay.

Guest favourite
A serene waterfront scene captures a vibrant sunset reflecting off calm waters. Silhouetted figures of an adult and child fish from the shore, surrounded by a natural landscape. Nearby, wooden chairs invite relaxation while the sky transitions from orange to deep blue.
Home in Reedville
4.93 out of 5 average rating, 178 reviews

Sunkissed Cottage-private, natural waterfront home

Want a cozy, private getaway surrounded by nature, lush trees, beautiful sunsets on the Little Wicomico? Sunkissed Cottage is cheerful home full of wonderful amenities! Enjoy drinking coffee on the porch watching the deer and birds. Take a 2 minute walk down our path through the woods to our waterfront where you can enjoy the water. Our home has high speed internet, smart tvs in every bedroom, corn hole boards, firepit and gas grill. The kitchen is well stocked for all your culinary needs.

Top Guest favourite
Cottage in Leonardtown
4.96 out of 5 average rating, 253 reviews

Beach Front and 'Perfectly Placed'

Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

Top Guest favourite
Two glasses of red wine are placed on a wooden tray next to a spa. A single rose with green leaves rests beside the glasses. Lush greenery surrounds the area, providing a natural backdrop.
Home in Dameron
4.99 out of 5 average rating, 134 reviews

Peace Point - Waterfront, Secluded, Home w/hot tub

Take a break and unwind at this peaceful oasis. Very quiet, and secluded waterfront getaway is the perfect spot to relax with nature. House is located approximately 150 feet from the creeks edge providing amazing views. Located on a very quiet and unpopulated creek (no other houses) off the Chesapeake Bay, our home offers a scenic deck with hot tub, waterfront fire pit with seating for up to six people, private floating dock with kayaks to explore the scenic creek.

Top Guest favourite
A circle of Adirondack chairs in white and black is set on a grassy area overlooking the water. Nearby, a fire pit is surrounded by tall grasses, and a dock is visible in the distance against a clear sky.
Guesthouse in Deal Island Historic District
4.98 out of 5 average rating, 48 reviews

Blue Crab Bungalow

Our charming bungalow allows you to relax, refresh and truly unwind while taking in views of the bay. ​ Enjoy amazing sunsets, lots of stars, and the water view from the 2nd story deck, private pier, or around the fire pit. Try crabbing or fishing from the pier. No license needed! A small local beach for swimming and public boat ramp are less than 5 minutes away. We are a little over an hour to Ocean City, Chincoteague, Assateague, and Blackwater Refuge.

Top Guest favourite
Two houseboats are positioned side by side on a boat lift, reflected in calm waters. The structure features a combination of wooden and grey exteriors, large windows, and porches. Lush trees and the warm hues of sunset provide a serene backdrop.
Houseboat in Solomons
4.98 out of 5 average rating, 174 reviews

Good Vibe Villa, Tiny houseboat

This tiny houseboat sits permanently on a boat lift, so you will have the unique experience of being over water without the risk of sea sickness! Located in the heart of quaint Solomons Island, this is a great stay if you love being near the water. Unparalleled views from your private porch. Please note, due to extensive pet damage we have changed this property to strictly no animals. You will be asked to leave if you arrive with a pet.

Top Guest favourite
A wooden boardwalk extends toward a sandy beach, flanked by tall grasses and wetlands. The peaceful water is visible in the distance under a clear blue sky, with a few clouds adding texture to the scene.
Cottage in Westover
4.99 out of 5 average rating, 252 reviews

Rumbley Cottage on the Tangier Sound-Private Beach

Rumbley Cottage, a custom-built home, provides a quiet stay in nature. Views from all windows. Look out at the mouth of the Manokin River at Tangier Sound on one side; wetlands on the other side. NO CLEANING OR PET FEE. Rumbley Cottage is enjoyed year- round with a great fireplace. WE PROVIDE THE FIREWOOD AND STARTERS. Many amenities including Molton Brown toiletries, kayaks, SPBs, bikes, beach equipment; well-stocked kitchen.

Guest favourite
A serene outdoor space features a tranquil waterfall pond, surrounded by lush greenery. Four wooden chairs invite relaxation, along with a small side table nearby. Stone pathways lead through the landscaped area, creating a peaceful atmosphere for outdoor gatherings.
Home in Salisbury
4.84 out of 5 average rating, 165 reviews

Highbanks House

Forget your worries in this spacious and serene space. Welcome to your dream home! This stunning 5-bedroom, 3-full-bath rancher is nestled on over 6 acres of private land, offering a perfect blend of comfort and nature. Located just 6 miles from downtown Salisbury and 8 miles from Salisbury University, this property provides both tranquility and convenience.

Top Guest favourite
Cottage in Smith Island
4.97 out of 5 average rating, 249 reviews

Levering Creek Cottage with private dock

Levering Creek Cottage is a waterfront property with a deep water dock that you can see from the back door. We are located on Levering Creek where you can sit on the dock watching watermen arrive with their daily catch, see nesting bald eagles, watch beautiful sunrise, fish and crab. We are also just steps away from most everything including the ferry.

Top Guest favourite
A single-story waterfront home is visible, featuring a light-colored exterior and dark shutters. A welcoming sign is positioned at the front, and a mature tree provides shade in the yard. A simple pathway leads to the entrance, surrounded by a low fence.
Home in Tangier
5 out of 5 average rating, 145 reviews

Island Oasis, Tangier Island, Virginia

Island Oasis is a one story, waterfront, newly renovated home situated in the heart of town. The tour boat docks are directly behind property with a gift shop on site. Restaurant, ice cream/sandwich deck, grocery store, church, museum , etc are all within walking distance. Guests will have full access to home and a nice deck overlooking harbor.

Popular amenities for Deal Island Historic District holiday rentals